Pyridine → 1,8-Bis[2-(diethylamino)acetamido]anthraquinone

HRID 556200Notes

Reaction equation

HRID 556200 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:21][C:22](=[O:25])[CH2:23]Cl)[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:4].[N:27]1[CH:32]=[CH:31]C=[CH:29][CH:28]=1.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>CN(C)C=O>[CH2:32]([N:27]([CH2:28][CH3:29])[CH2:2][C:3]([NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:21][C:22](=[O:25])[CH2:23][N:35]([CH2:36][CH3:37])[CH2:33][CH3:34])[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:4])[CH3:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8021DiethylamineHCID 469280411,8-Bis(chloroacetamido)anthraquinone2×

Product 1

HCID 462447751,8-Bis[2-(diethylamino)acetamido]anthraquinoneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 0.4 g, 1.0 mmol 1,8-bis(chloroacetamido)anthraquinone (compound 3) with pyridine (0.5 ml), and 0.6 ml, 6 mmole Diethylamine, dissolved in 20 ml dehydrated dimethylformamide (DMF). The mixture is reacted in a mini-reactor. The reaction temperature is 120° C. in the oil bath and the reaction time is 30 minutes. The reacted mixture is poured into 50 ml ice water and is filtered to collect precipitate. The precipitate is recrystallized from ethanol to get yellow compound 3l.

Workup

  1. customThe mixture is reacted in a mini-reactor
  2. customis 120° C. in the oil bath
  3. filtrationis filtered
  4. customto collect precipitate
  5. customThe precipitate is recrystallized from ethanol

Sources & evidence

ORD record
ord-7fa87425d52c47a5b3831c9a71c45e7e
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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